771-60-8

Basic information

• Product Name: 2,3,4,5,6-Pentafluoroaniline
• Synonyms: Aminopentafluorobenzene;Aniline, 2,3,4,5,6-pentafluoro-;Pentafluorophenylamine;PENTAFLUOROANILINE;PENTAFLUORANILINE;2,3,4,5,6-PENTAFLUOROBENZENAMINE;2,3,4,5,6-PENTAFLUOROANILINE;pentafluronitrobenzene
• CAS NO: 771-60-8
• Molecular Formula: C₆H₂F₅N
• Molecular Weight: 183.08
• EINECS: 212-234-2
• Product Categories: Aniline;Fluorobenzene;Amines;C2 to C6;Nitrogen Compounds;organofluorine compounds
• Mol File: 771-60-8.mol

Chemical Properties

• Melting Point: 33-35 °C(lit.)
• Boiling Point: 153 °C(lit.)
• Flash Point: 165 °F
• Appearance: White to salmon/Crystalline Low Melting Solid
• Density: 1,744 g/cm3
• Vapor Pressure: 3.69mmHg at 25°C
• Refractive Index: 1.429
• Storage Temp.: Store below +30°C.
• Solubility: toluene: soluble
• PKA: -0.16±0.10(Predicted)
• Water Solubility: Soluble in toluene, and organic solvents. Insoluble in water.
• BRN: 1819387
• CAS DataBase Reference: 2,3,4,5,6-Pentafluoroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,5,6-Pentafluoroaniline(771-60-8)
• EPA Substance Registry System: 2,3,4,5,6-Pentafluoroaniline(771-60-8)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-36/37/39
• WGK Germany: 3
• RTECS: BY7920000
• TSCA: T
• HazardClass: IRRITANT
• Hazardous Substances Data: 771-60-8(Hazardous Substances Data)

Usage

Uses

Used in Catalyst Preparation:
2,3,4,5,6-Pentafluoroaniline is used as a precursor for the preparation of pentafluorophenylammonium triflate, an efficient catalyst for esterification and thioesterification processes. Its unique chemical properties make it a valuable component in these reactions.
Used in Synthesis of Titanium Complexes:
In the field of coordination chemistry, 2,3,4,5,6-pentafluoroaniline is used in the synthesis of various titanium complexes with two anionic [N, O-] bidentate salicylaldiminato ligands. These complexes have potential applications in various industrial processes.
Used in Pharmaceutical Applications:
2,3,4,5,6-Pentafluoroaniline forms metal-drug complexes, such as cis-Pt-(2,3,4,5,6-pentafluoroaniline)2-Br2, which have been tested against the promastigote forms of Leishmania donovani, a parasite responsible for leishmaniasis. This indicates its potential use in the development of new drugs to combat this disease.

Safety Profile

Poison by intraperitoneal route. When heated to decomposition it emits very toxic fumes of Fí and NOx.

InChI:InChI=1/C6HF5O/c7-1-2(8)4(10)6(12)5(11)3(1)9/h12H

Upstream product

• 392-56-3 Hexafluorobenzene 
• 880-78-4 pentafluoronitrobenzen 
• 287-92-3 Cyclopentane 
• 1423-15-0 perfluorophenyl azide 
• 116-83-6 1-amino-4-methoxyanthraquinone 
• 80600-73-3 C₆F₅NH^(1-)*Na⁽¹⁺⁾=C₆F₅NHNa 
• 143896-70-2 N-(2,3,4,5,6-pentafluorophenyl)-1-phenylmethanimine 
• 82-45-1 1-amino-9,10-anthracenedione 
• 105608-97-7 N-pentafluorophenylhydroxylamine 
• 80684-62-4 F-benzohydroxamic acid 
• 97580-75-1 bis(α-pentafluoroanilino-2,3,4,5,6-pentafluorobenzyl)peroxide 
• 108-88-3 toluene 
• 36375-78-7 pentafluorophenyl nitrene 
• 7664-41-7 ammonia 

Downstream Products

• 23188-59-2 (pentafluorophenyl)N(SiMe₃)2 
• 25751-28-4 1,1,3,3,5,5,7,7-octamethyl-2,6-bis(pentafluorophenyl)-cyclo-1,3,5,7-tetrasila-2,6-diaza-4,8-dioxane 
• 24735-63-5 N-Pentafluorphenyl-1.1.3.3.5.5-hexamethylcyclotrisil-6-aza-2.4-dioxan 
• 23188-63-8 2,2,4,4,6,6,8,8,10,10,12,12-Dodecamethyl-5,11-bis-pentafluorophenyl-1,3,7,9-tetraoxa-5,11-diaza-2,4,6,8,10,12-hexasila-cyclododecane 
• 14747-47-8 N-trimethyl-B-tris(pentafluorophenylamino)borazine 
• 23188-60-5 N,N'-Di-pentafluorphenyl-tetramethyl-cyclodisilazan 
• 23188-64-9 N,N',N''-Tri-pentafluorphenyl-hexamethyl-trisilazan 
• 23188-61-6 N_.N'-Di-pentafluorphenyl-tetraphenyl-cyclodisilazan 
• 64317-34-6 N-(pentafluorophenyl)carbonimidoyl dichloride 
• 58751-08-9 2,3,4,5,6-pentafluoroformanilide 
• 80588-46-1 N-(2,3,5,6-tetrafluoropyrid-4-yl)pentafluoroaniline 
• 31478-75-8 N-phenyltetrafluorobenzoxazole 
• 28078-83-3 N-pentafluorophenylbenzamide 
• 784-14-5 2,3,4,5,6-pentafluorobiphenyl 

Relevant articles and documents

Observation of an isolated intermediate of the nucleophilic aromatic substition reaction by infrared spectroscopy

(Figure Presented) Caught in the act: The σ complex formed as an intermediate in a nucleophilic aromatic substitution has been observed experimentally. Efficient direct ionization of C6F6 by coherent vacuum ultraviolet light was employed to effect the formation of C 6F5NH2 + from C6F 6 +/NH3. Comparison of the IR spectrum of (C6F6-NH3)+ with that predicted from DFT calculations showed that the cluster cation forms a stable σ complex (see picture).

Syntheses of Transition Metal Complexes of Pentafluorophenylhydrazine

By reaction of pentafluorophenylhydrazine with metal chlorides the complexes M(NH2NHC6F5)4Cl2 (M = Co, Ni), M(NH2NHC6F5)2Cl2 (M = Mn, Fe, Pd, Zn,

Biorenewable carbon-supported Ru catalyst for: N -alkylation of amines with alcohols and selective hydrogenation of nitroarenes

Herein, we developed a renewable carbon-supported Ru catalyst (Ru/PNC-700), which was facilely prepared via simple impregnation followed by the pyrolysis process. The prepared Ru/PNC-700 catalyst demonstrated remarkable catalytic activity in terms of conversion and selectivity towards N-alkylation of anilines with benzyl alcohol and chemoselective hydrogenation of aromatic nitro compounds. In addition, local anesthetic pharmaceutical agents (e.g., butamben and benzocaine), including key drug intermediates, were synthesized in excellent yields under mild conditions and in the presence of water as a green solvent. Moreover, the prepared Ru/PNC-700 catalyst could be easily recovered and reused up to five times without any apparent loss in activity and selectivity.

Borane Adducts of Hydrazoic Acid and Organic Azides: Intermediates for the Formation of Aminoboranes

The reaction of HN3 with the strong Lewis acid B(C6F5)3 led to the formation of a very labile HN3?B(C6F5)3 adduct, which decomposed to an aminoborane, H(C6F5)NB(C6F5)2, above ?20 °C with release of molecular nitrogen and simultaneous migration of a C6F5 group from boron to the nitrogen atom. The intermediary formation of azide–borane adducts with B(C6F5)3 was also demonstrated for a series of organic azides, RN3 (R=Me3Si, Ph, 3,5-(CF3)2C6H3), which also underwent Staudinger-like decomposition along with C6F5 group migration. In accord with experiment, computations revealed rather small barriers towards nitrogen release for these highly labile azide adducts for all organic substituents except R=Me3Si (m.p. 120 °C, Tdec=189 °C). Hydrolysis of the aminoboranes provided C6F5-substituted amines, HN(R)(C6F5), in good yields.

Coordination or Oxidative Addition? Activation of N-H with [Tp′Rh(PMe3)]

A thermal reaction of amines, anilines, and amides with Tp′Rh(PMe3)(CH3)H (1, Tp′ = tris(3,5-dimethyl-pyrazolyl)borate) is described in this report. No N-H bond cleavage was observed for reactions between ammonia or unsubstituted aliphatic amines with the reactive fragment [Tp′Rh(PMe3)]. Instead, amine coordination products (κ2-Tp′)Rh(PMe3)(NHR1R2) (R1 = H, R2 = H, nPr, iPr, octyl; R1 = R2 = Et; R1, R2: pyrrolidine) were observed, and the crystal structure of (κ2-Tp′)Rh(PMe3)(NH2iPr) is reported. No coordination products were observed when 1 was reacted with 1,1,1,3,3,3-hexafluoropropan-2-amine, anilines, and amides. Instead, the oxidative addition products (κ3-Tp′)Rh(PMe3)(NHR)H (R = CH(CF3)2, C6H5, 3,5-dimethylbenzyl, C6F5, C(O)CH3, C(O)CF3) were observed. Both RhI-N coordination products (κ2-Tp′)Rh(PMe3)(NH2CH2CF3) and RhIII N-H addition products (κ3-Tp′)Rh(PMe3)(NHCH2CF3)H were generated when 1 was reacted with 2,2,2-trifluoroethylamine. Coordination products dissociate ammonia and amines in benzene much faster than oxidative addition products eliminate anilines and amides. The relative metal-nitrogen bond energies were studied using established kinetic techniques. Analysis of the relationship between the relative M-N bond strengths and N-H bond strengths showed a linear correlation with a slope = RM-N/N-H of 0.91 (10), indicating that the Rh-N bond strength varies in direct proportion to the N-H bond strength.

Preparation method of polyfluoroaniline

The invention relates to a preparation method of polyfluoroaniline, according to the method, the polyfluoroaniline is prepared by a two-step common reaction from polyfluorobenzene as a raw material, the method has the characteristics of low reaction temperature, small pressure, low cost, and the like, is suitable for industrial production application, and is convenient for large-scale production;the polyfluoroaniline product obtained by the method has less impurities and high product purity.

Preparation method for pentafluorophenol

The invention relates to the field of organic synthesis and especially relates to a preparation method for pentafluorophenol. The preparation method comprises the steps of: 1) a Hoffmann rearrangement reaction: performing the rearrangement reaction to the compound (II) in the presence of alkali and a halogenation reagent to prepare the compound (III); 2) a diazo-hydrolysis reaction: performing a diazotization reaction to the compound (III) with a nitroso compound and performing a hydrolysis reaction in the presence of a catalyst to prepare the compound (I). The raw materials in the method are easy to obtain. The preparation method is short in synthesis route and is mild in reaction conditions, is simple in purification of the product, has high product purity and stable product quality, is low in cost of the whole synthesis route and is suitable for industrial large-scale promotion and application.

Enhanced chemoselective hydrogenation through tuning the interaction between pt nanoparticles and carbon supports: Insights from identical location transmission electron microscopy and x?ray photoelectron spectroscopy

Ultrasmall-sized platinum nanoparticles (Pt NPs) (～1 nm) supported on carbon nanotubes (CNTs) with nitrogen doping and oxygen functional groups were synthesized and applied in the catalytic hydrogenation of nitroarenes. The advanced identical location transmission electron microscopy (IL-TEM) method was applied to probe the structure evolution of the Pt/CNT catalysts in the reaction. The results indicate that Pt NPs supported on CNTs with a high amount of nitrogen doping (Pt/H-NCNTs) afford 2-fold activity to that of Pt NPs supported on CNTs with oxygen functional groups (Pt/oCNTs) and 4-fold to that of the commercial Pt NPs supported on active carbon (Pt/C) catalyst toward nitrobenzene. The catalytic performance of Pt/H-NCNTs remained constant during four cycles, whereas the activity of the Pt/oCNTs was halved at the second cycle. Compared with Pt/oCNTs, Pt/H-NCNTs exhibited a higher selectivity (>99%) in chemoselective hydrogenation of halonitrobenzenes to haloanilines due to the electron-rich chemical state of Pt NPs. The strong metal?support interaction along with the electron-donor capacity of nitrogen sites on H-NCNTs are capable of stabilizing the Pt NPs and achieving related catalytic recyclability as well as approximately 100% selectivity. The catalyst also delivers exclusively selective hydrogenation toward nitro groups for a wide scope of substituent nitroarenes into their corresponding anilines.

The colloidal synthesis of unsupported nickel-tin bimetallic nanoparticles with tunable composition that have high activity for the reduction of nitroarenes

Abstract Ni-Sn bimetallic nanoparticles with controllable size and composition were prepared by facile method in ambient air using inexpensive metal salts. Adjusting stoichiometric ratio of Ni and Sn precursors afforded nanoparticles with different compositions, such as Ni100, Ni74-Sn26, Ni59-Sn41, and Ni50-Sn50. The characterization of nanoparticles was performed by powder X-ray diffraction (XRD), transmission electron microscopy (TEM), high resolution transmission electron microscopy (HR-TEM), and energy dispersive X-ray analysis (EDX). Ni75-Sn25 and Ni60-Sn40 nanoparticles showed enhanced catalytic activity towards 2-nitroaniline reduction as compared with Ni nanoparticles. Furthermore, Ni75-Sn25 nanocatalyst exhibited excellent activity for the reduction of a number of nitro aromatic compounds under mild conditions along with high level of reusability.

Efficient and highly selective boron-doped carbon materials-catalyzed reduction of nitroarenes

Exploring the potential catalytic applications of boron-doped carbon materials is a fascinating challenge. Here we describe that boron-doped onion-like carbon and carbon nanotubes as metal-free catalysts exhibit excellent catalytic activity and stability in nitroarene reduction under a stoichiometric amount of reductant.